Synthesis and Absolute Configuration of Hyperaspine, an Alkaloid of the Ladybird <i>Hyperaspis campestris</i>

Abstract

Abstract Hyperaspine ( 1a ), isolated from the European Coccinellidae Hyperaspis campestris , isthe first representative of a new type of ladybird alkaloids having a 3‐oxaquinolizidine skeleton. A new total synthesis of (±)‐hyperaspine starting from protected piperidin‐4‐one has been achieved. The absolute configuration of the natural alkaloid was unequivocally established to be 3 S ,4a S ,6 R ,8 S by HPLC analyses on a chiral column. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2005)